Jeffrey Toobin: Drama in the court

In his second book about the inner workings of the Supreme Court, Jeffrey Toobin sheds light on high-stakes legal battles between the White House and Chief Justice John Roberts.

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The O.J. Simpson trial gave Jeffrey Toobin his TV career breakthrough. “Before that there was no such thing as a TV legal analyst,” he said. Toobin is seen here in the CNN lunchroom in New York City. He also is legal correspondent for the New Yorker magazine.

Photo: Kelly Guenther, Special to the Star Tribune

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NEW YORK -- At CNN's bureau in the Time Warner building on Columbus Circle, Jeffrey Toobin is a cubicle nomad. In between his 8 a.m. stand-up to discuss updates in the Penn State and Trayvon Martin cases, and his 11 a.m. studio sitdown with Ashleigh Banfield to talk about the shootings at a movie theater in Aurora, Colo., he hops from PC to PC, checking and sending e-mails and posting blog items.

Lacking his own desk at the cable-TV offices, Toobin at one point forgets where he left his briefcase, but remains unfazed. When he and Banfield launch into their on-camera banter, his analysis comes so quickly and effortlessly, it wouldn't be surprising if he were simultaneously composing his next Tweet in his head.

Toobin's career demands multitasking at almost every moment. He juggles three jobs in the same field -- legal correspondent for both CNN and the New Yorker, and author of several books, including 2007's best-selling Supreme Court narrative "The Nine."

His latest, "The Oath: The Obama White House and the Supreme Court" (on sale Tuesday), examines several tumultuous years at the nation's highest court, from Chief Justice John Roberts' muffing his lines during Obama's oath of office in 2008 to the landmark Citizens United controversy to the surprise conclusion of the closely watched health-care decision in June, over which Toobin had to eat a rather large crow.

Toobin comes to St. Paul Sept. 26 as a speaker for the Talking Volumes series.

On this typical Toobin workday, you have to walk fast if you want to keep up.

"Lawyers sometimes benefit from mystifying what they do, and the advantage of knowing a subject well is the ability to say, it's actually not that complicated, and here's what matters," said Toobin, a Harvard-educated former prosecutor, as he expertly wiped all traces of orange-tinted makeup from his face before heading out to hop a subway to Times Square and the New Yorker offices, where at least he gets his own cubbyhole (other writers have to share).

"The Oath" is Toobin's second book about the Supreme Court. His first, "The Nine," offered a telling behind-the-scenes look at Bush v. Gore. It also humanized the justices, revealing idiosyncrasies and eccentricities usually cloaked by the black robes of secrecy.

"What appeals to me about writing about the [Supreme] Court is that everyone knows it's important, but there are few opportunities to learn who these people are," he said. "The public doesn't hear more about it because the people who care deeply tend to be strong partisans, like those on either side of Roe v. Wade. I don't feel evangelical about telling people what to think, but the court is awfully important."

Over lunch at the trendy Condé Nast cafeteria, Toobin led a game of "guess the magazine," matching diners and workplaces according to their body types and outfits. As a lanky guy in a form-fitting blazer paired with matching shorts and wingtips glided past, he said, "Bet you don't see that at the Star Tribune."

Obama v. Roberts

"The governing idea behind the book is that there is a contest going on between John Roberts and Barack Obama about the future of the law in the U.S.," he said. "What makes that so compelling is they're both such intelligent, charismatic, formidable people."

The cover features headshots of Obama and Roberts in profile, both with determined expressions that radiate a "not gonna budge" vibe.

Toobin views Roberts as the more radical of the two, because he seems bent on making sweeping changes that tilt the court toward even more conservatism, while Obama appears more cautious.

The parties have switched places since the 1960s, he writes in "The Oath." "Then, it had been the Democrats who were the activists, striking down laws that were not to their liking. Now, it was the Republicans."

He said he was "completely, utterly surprised" when Roberts defied predictions -- notably Toobin's own -- and sided with Obama and the court's liberal justices on health care, ensuring that a major part of the president's legacy thus far would be saved.

At the end of March, Toobin caught a lot of Chicken Little flak for calling the case's oral arguments a "train wreck" for Obama, then announcing on CNN and Twitter that the law was likely to be struck down, causing a chain reaction of pundit retweets and liberal panic. He later had to utter mea culpas all over the place, including on national television.

This end-of-session plot twist also sent Toobin scrambling against deadline to tack three more chapters to the end of "The Oath" Still, he said, the Citizens United hearing, in which the high court declined to revisit its blockbuster 2010 decision allowing unlimited corporate and union campaign donations, remains the book's centerpiece.

"Bush v. Gore was the pivot on which 'The Nine' turned," he said. "When I started this book, I was worried there weren't going to be any cases of similar interest and I was fortunate -- I don't know if the country was fortunate -- to get such a significant case right off the top."

Citizens United "gave the book purpose and worked well dramatically," he said, allowing him to introduce Elena Kagan, and outline the significance of it being Sonia Sotomayor's first case on the bench and John Paul Stevens' last.

Although Toobin himself has said, "I'm not exactly famous for my hatred of the Obama administration," he has been sharply critical of what he sees as the president's neglecting to make lower-court appointments.

"Obama's judicial appointments have been few and cautious," he said. "It is inconceivable to me that a president would sacrifice the opportunity to leave a legacy of lifetime appointments to the lower federal courts, but it's just not a priority for Obama."

A flirtation with fiction

Toobin is a master sourcer. He has spoken to a majority of the Supreme Court's living justices, and more than 40 law clerks on condition of anonymity. He makes Byzantine bureaucracy and case law comprehensible, and laces suspense into proceedings that move at a glacial pace.

Before "The Nine," Toobin's book subjects, including the Clinton sex scandal and the O.J. Simpson trial, were the types of stories that naturally grip the public's interest. "The Supreme Court, not so much," he said.

But something happened in the summer of 2004 to make him seriously consider the topic. That was when he decided to try his hand at a legal thriller, about the murder of a morning-show anchor captured on live TV and the subsequent manhunt and prosecution. Legendary editor Phyllis Grann read his first three chapters, and invited him to her home.

"She gave me a Diet Coke and said, 'This novel is awful. You should stop. Instead, you should write a book about the Supreme Court.'" There hadn't been a real behind-the-scenes look at the court since 1979's 'The Brethren,' and he'd already profiled several of the justices, "so I swallowed my disappointment. Some people can write fiction and some can't, and evidently I'm in the latter group."

Fans and critics

John Bennet, Toobin's editor at the New Yorker, says that the writer's understanding of people, more than his understanding of the law, is what makes his work stand out.

"That's why he can write with equal brilliance about the personality clashes that affect the Supreme Court and the seemingly ordinary disputes, among ordinary people, that make their way into our legal system," Bennet said.

Considered enough of a celebrity to have a profile on Fameball.com, Toobin, 52, and married to his college sweetheart Amy McIntosh for 26 years, has seen his private life undergo more scrutiny than is comfortable. He has been the target of some pointed snark on media-gossip blogs, most prominently for fathering a child with another woman in 2009. But he has his high-profile fans, as well. Gene Weingarten, columnist for the Washington Post, recently tweeted that he had "a mancrush on Toobs. Nerdsmarts coupled w/restrained but sassy Jewfro."

Larry Jacobs, a political science expert at the University of Minnesota, calls Toobin "a keen observer of the court who is still wiping egg from his face [over his wrong guess on the health care ruling]. It is a sign of Toobin's standing that he got so much attention. Whether his predictions enjoy the same level of respect is another question."

David Lillehaug, a former U.S. attorney now with Fredrikson & Byron who represented both Sen. Al Franken and Gov. Mark Dayton in their election vote recounts, begs to differ. He has read several of Toobin's books, and thinks highly of his work.

"The recount book is my favorite, I consider it to be the definitive account of Bush v. Gore," he said. "I read it in anticipation of Franken-Coleman and it was influential in our strategy."

Minneapolis attorney Andy Luger, who worked with Toobin in the early 1990s when they were assistant U.S. district attorneys, says fame and celebrity haven't changed his friend. When he sees Toobin on CNN, "it's the same guy I sat with in a Brooklyn diner 20 years ago."

Toobin predicts next year will be a dramatic one for the court. He foresees some "very conservative decisions about civil rights and affirmative action in higher education." Also, "the core of the Voting Rights Act will likely be overturned." What's less certain, he said, is the fate of the Defense of Marriage Act.

"I think equal treatment for gay people is an idea that at least some conservatives on that court may well accept. But any sort of racial preferences are doomed."

Unbowed by his stumble last spring, Toobin still forecasts the future with aplomb.

Kristin Tillotson • 612-673-7046

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